(R)-2-hydroxy-2-(1',2',3',4'-tetrahydro-1',1',4',4'-tetramethyl-6'-naphthalenyl)acetic acid | 262433-62-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (R)-2-hydroxy-2-(1',2',3',4'-tetrahydro-1',1',4',4'-tetramethyl-6'-naphthalenyl)acetic acid
• 英文别名: (R)-2-hydroxy-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)acetic acid；(2R)-2-hydroxy-2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)acetic acid
• CAS: 262433-62-5
• 化学式: C₁₆H₂₂O₃
• 分子量: 262.349
• InChiKey: RMZVGANQMYNRAL-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-2-hydroxy-2-(1',2',3',4'-tetrahydro-1',1',4',4'-tetramethyl-6'-naphthalenyl)acetic acid 在 草酰氯 作用下， 生成 4-[2-chloro-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-acetylamino]-3-fluoro-benzoic acid methyl ester
  参考文献：
  名称：

  缺电子的N-亚磺酰基苯胺与手性α-羟基酸的反应：对映体纯α-羟基酰胺合成的新方法

  摘要：

  已经开发了一种通过N-亚磺酰基苯胺衍生物从手性α-羟基酸和电子缺陷型苯胺制备对映体纯的α-羟基酰胺的实用方法。

  DOI：

  10.1016/s0040-4039(00)01011-x
• 作为产物：
  描述：

  2-oxo-2-(1',2',3',4'-tetrahydro-1',1',4',4'-tetramethyl-6'-naphthalenyl)acetic acid 在 葡萄糖 、 Candida utilis SC 13983 作用下， 以 甲醇 、 phosphate buffer 为溶剂， 以64%的产率得到(R)-2-hydroxy-2-(1',2',3',4'-tetrahydro-1',1',4',4'-tetramethyl-6'-naphthalenyl)acetic acid
  参考文献：
  名称：

  Enantioselective microbial reduction of 2-oxo-2-(1′,2′,3′,4′-tetrahydro-1′,1′,4′,4′-tetramethyl-6′-naphthalenyl)acetic acid and its ethyl ester

  摘要：

  The chiral ester ethyl (2R)-hydroxy-2-(1',2',3',4'-tetrahydro-1',1',4',4'-tetramethyl-6'-naphthalenyl) acetate 2 and the corresponding acid 4 were prepared as intermediates in the synthesis of the retinoic acid receptor gamma-specific agonist (R)-3-fluoro-4-[[hydroxy(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)acety]amino]benzoic acid 7. Enantioselective reduction of ethyl 2-oxo-2-(1',2',3',4'-tetrahydro-1'.1',4',4'-tetramethyl-6'-naphthalenyl)acetate 1 to alcohol 2 was carried out using Aureobasidium pullulans SC 13849 in 98% yield and with an enantiomeric excess (e.e.) of 96%. Among microorganisms screened for the reduction of 2-oxo-2-(1',2',3',4'-tetrahydro-1',1',4',4'-tetramethyl-6'-naphthalenyl)acetic acid 3 to hydroxy acid 4. Candida maltosa SC 16112 and two strains of Candida utilis (SC 13983, SC 1394) gave reaction yields of >53% with e.e.s. of >96%. (C) 2002 Elsevier Science Ltd, All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00109-x

文献信息

• A Practical Synthesis of the RAR_γ Agonist, BMS-270394
  作者：Ramakrishnan Chidambaram、Joydeep Kant、Jason Zhu、Jean Lajeunesse、Pierre Sirard、Peter Ermann、Peter Schierling、Peter Lee、David Kronenthal

  DOI：10.1021/op0202134

  日期：2002.9.1

  A novel synthesis of 1 (BMS-270394), a nuclear retinoic acid receptor (RARgamma) agonist, is reported. The synthesis includes an enantioselective reduction of alpha-ketoacid 4 to the corresponding chiral a.-hydroxy acid 7 using a NaBH4/L-tartaric acid mixture and a novel coupling between 7 and an electron-deficient aniline 11 which was activated via N-sulfinyl derivative 15 to form chiral alpha-hydroxy amide 16. The synthesis was completed by a racemization-free hydrolysis of 16 to the corresponding alpha-hydroxy amidoacid 1 using KOPSiMe3 in acetonitrile.
• US6331570B1
  申请人：——

  公开号：US6331570B1

  公开（公告）日：2001-12-18
• Reaction of electron-deficient N-sulfinylanilines with chiral α-hydroxy acids: a new process for the synthesis of enantiomerically pure α-hydroxy amides
  作者：Ramakrishnan Chidambaram、Jason Zhu、Kumar Penmetsa、David Kronenthal、Joydeep Kant

  DOI：10.1016/s0040-4039(00)01011-x

  日期：2000.8

  A practical procedure to prepare enantiomerically pure α-hydroxy amides from chiral α-hydroxy acids and electron-deficient anilines via N-sulfinylaniline derivatives has been developed.

  已经开发了一种通过N-亚磺酰基苯胺衍生物从手性α-羟基酸和电子缺陷型苯胺制备对映体纯的α-羟基酰胺的实用方法。
• Enantioselective microbial reduction of 2-oxo-2-(1′,2′,3′,4′-tetrahydro-1′,1′,4′,4′-tetramethyl-6′-naphthalenyl)acetic acid and its ethyl ester
  作者：Ramesh N Patel、Linda Chu、Ramakrishna Chidambaram、Jason Zhu、Joydeep Kant

  DOI：10.1016/s0957-4166(02)00109-x

  日期：2002.3

  The chiral ester ethyl (2R)-hydroxy-2-(1',2',3',4'-tetrahydro-1',1',4',4'-tetramethyl-6'-naphthalenyl) acetate 2 and the corresponding acid 4 were prepared as intermediates in the synthesis of the retinoic acid receptor gamma-specific agonist (R)-3-fluoro-4-[[hydroxy(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)acety]amino]benzoic acid 7. Enantioselective reduction of ethyl 2-oxo-2-(1',2',3',4'-tetrahydro-1'.1',4',4'-tetramethyl-6'-naphthalenyl)acetate 1 to alcohol 2 was carried out using Aureobasidium pullulans SC 13849 in 98% yield and with an enantiomeric excess (e.e.) of 96%. Among microorganisms screened for the reduction of 2-oxo-2-(1',2',3',4'-tetrahydro-1',1',4',4'-tetramethyl-6'-naphthalenyl)acetic acid 3 to hydroxy acid 4. Candida maltosa SC 16112 and two strains of Candida utilis (SC 13983, SC 1394) gave reaction yields of >53% with e.e.s. of >96%. (C) 2002 Elsevier Science Ltd, All rights reserved.